4,6-Dichloropyrimidine → HCID 53257559, compound

HRID 576678Notes

Reaction equation

HRID 576678 reaction equation
[N:1]1([CH2:10][C:11]2[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:18][C:19]1[N:20]=[CH:21][N:22]=[C:23]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[CH:12]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 43134808HCID 43134808, compound

Product 1

HCID 53257559HCID 53257559, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.077 g 3-Indol-1-ylmethyl-phenylamine (obtained in Step 2, 4.84 mmol) and 0.722 g 4,6-dichloropyrimidine (4.84 mmol) was dissolved in 50 cm3 of isopropyl-alcohol, 1.27 cm3 N,N-diisopropyl-ethylamine (0.939 g, 7.27 mmol) were added and the mixture was refluxed for three days. Then the mixture was evaporated under reduced pressure, 100 cm3 of water was added and it was extracted with 3×70 cm3 ethyl-acetate. Combined organic layer was washed with brine, dried over MgSO4 and evaporated to a yellowish oil. The residue was crystallized from minimal amount of acetonitrile and washed with diethyl-ether to give the desired product as an off-white solid. Overall yield for Step 2 and Step 3: 1.015 g (63%). For analitical results and compound identification see Table 1. The compound was used as a starting material in the preparation of Example 91.

Workup

  1. temperaturethe mixture was refluxed for three days
  2. customThen the mixture was evaporated under reduced pressure, 100 cm3 of water
  3. additionwas added
  4. extractionit was extracted with 3×70 cm3 ethyl-acetate
  5. washCombined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated to a yellowish oil
  8. customThe residue was crystallized from minimal amount of acetonitrile
  9. washwashed with diethyl-ether

Sources & evidence

ORD record
ord-175f25794ec14aada4be40bcb1d699fa
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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